98050-72-7

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 39562-16-8 ethyl (Z)-2-(3-nitrobenzylidene)-3-oxobutanoate 
• 98064-08-5 5-(ethoxycarbonyl)-6-hydroxy-2,6-dimethyl-4-(m-nitrophenyl)-1,4,5,6-tetrahydropyrimidine 
• 39562-16-8 ethyl 2-(3-nitrophenylmethylene)-3-oxobutanoate 
• 124-42-5 acetamidine hydrochloride 

Downstream Products

• 98050-91-0 1-Acetyl-2,4-dimethyl-6-(3-nitro-phenyl)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 98050-84-1 3,5-bis(ethoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-3,4-dihydropyrimidine 
• 143996-62-7 2,4-Dimethyl-6-(3-nitro-phenyl)-pyrimidine-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Studies on cerebral protective agents. I. Novel 4-arylpyrimidine derivatives with anti-anoxic and anti-lipid peroxidation activities

Novel 4-arylpyrimidine derivatives were synthesized by the oxidation of 4-aryl-1,4-dihydropyrimidines, and their effects on anti-anoxic (AA) activity in mice and anti-lipid peroxidation (ALP) activity in rat brain mitochondria were investigated. Among these compounds, ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (4b) has AA activity (10mg/kg, i.p.) and ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4f) has ALP activity (73% inhibition at 10-5 g/ml). The latter compound (100mg/kg, i.p.) was also effective on arachidonate-induced cerebral edema in rats with comparable potency to that of vitamin E.

Synthesis of Novel Dihydropyrimidines and Tetrahydropyrimidines

Condensation of alkyl 2-acetyl-3-aryl-2-propenoate with acetamidine, benzamidine, guanidine, or 1,1-dimethylguanidine followed by dehydration of the resulting compound 2 with p-TsOH or Al2O3 gave 1,4(3,4)-dihydropyrimidine 3.Regioselective alkoxycarbonylation, acylation, and alkylation of compound 3 with alkyl chloroformate, acyl halide, or alkyl halide in the presence of NaH afforded the series of novel N-substituted 3,4-dihydropyrimidines 4, 5, and 6 in good yield.Stereoselective NaBH4 reduction of the 3,4-dihydropyrimidine hydrochloride 4 provided a singlestereoisomer of 1,2,3,4-tetrahydropyrimidine 7 whose stereochemistry was assigned as cis by X-ray crystallographic analysis.Conversely, the same reduction of the HCl salts of 3 or 6 gave a cis-trans mixture of tetrahydropyrimidines 8.